Middleburg, Virginia Bed and Breakfasts
Home > Find a B&B > By City > Middleburg, Virginia
Browse among the delightful array of quaint shops and inns. There are approximately 600 people currently residing in the town. Established in 1787 by Revolutionary War Lieutenant Colonel and Virginia statesman, Levin Powell, he purchased the land for Middleburg at $2.50 an acre from Joseph Chinn, first cousin to George Washington. Previously called "Chinn's Crossroads," Powell chose the name Middleburg because of the town's location midway between Alexandria and Winchester on the Ashby Gap trading route (now Route 50).
Since the 1730s, Middleburg had been a staging point for weary travelers along the Ashby Gap Road. The legacy of the colonial era continues today at Middleburg's charming inns that provide first rate accommodations to visitors from around the world. There are several inns located within the corporate limits, including the historic Red Fox Inn and Tavern. It is billed as the "oldest original inn in America". The Red Fox Tavern was a meeting spot for Confederate Colonel John Mosby and his Rangers. A century later, President Kennedy's press secretary, Pierre Salinger, held press conferences at the Red Fox in the Jeb Stuart Room.
Across the street is another gracious reminder of the past - the Windsor House Inn, circa 1824. During the Civil War, it was known as the Colonial Inn; and, was run by Catherine Broun. Although Catherine sympathized with the South, she generously served meals to Union troops at the inn as well when they occupied Middleburg in 1862.
See Inns in and near Middleburg: Downtown | 1 Mile | 5 Miles | 15 Miles | 25 Miles | 50 MilesMiddleburg Country InnDistance from city center: less than 1 milePhone: 540-687-6082 Toll Free: 800-262-6082 The Middleburg Country Inn is located at the foothills of Virginia's horse and wine country.Our bedrooms feature exquisite regional decor and include all the conveniences of modern living.A full country breakfast, cooked to order, is served daily.We promise a vacation you will never forget. Middleburg, Virginia View Listing Website |
|
![]() |
Briar Patch B&B InnDistance from city center: 10 mile(s)Phone: 703-327-5911 Toll Free: 866-327-5911 Historic farm (1805) on 47 rolling acres with great mountain views in the heart of VA horse and wine country. Large pool and hot tub. Antique decorated bedrooms in main house and a cozy one-bedroom cottage. We host weddings, meetings, and parties. Middleburg, Virginia View Listing Website |
Other Area Inns
![]() |
![]() Berryville InnDistance from city center: 14 mile(s)Phone: 540.955.0984 Office Toll Free: 540.336.3469 Mobile Known as the perfect Virginia getaway, our elegant European contemporary B&B provides thoughtful touches of unsurpassed guest comfort. Visit us in the Historic District, easy to locate and park, within a two block stroll to downtown activities and 5 star restaurants. Berryville (Middleburg), Virginia View Listing Website |
![]() |
![]() The Ashby Inn & RestaurantDistance from city center: 15 mile(s)Phone: 540-592-3900 Toll Free: 866-336-0099 The 1829 Ashby Inn & Restaurant is nestled in the quiet village of Paris, Virginia. Just one hour west of Washington, DC, the Inn is located within minutes from over one dozen wineries, the Appalachian Trail, and the quaint towns of Upperville and Middleburg. Paris (Middleburg), Virginia View Listing Website |






